Pressly 'would love to play' with Bregman again if former teammate signs with Cubs

MESA, Ariz. -- Cubs pitcher Jameson Taillon paused, considered his answer and cracked a smile, eliciting some laughter from the group of reporters and cameras surrounding his locker. He had just been asked about the possibility of free agent Alex Bregman being the next marquee addition for the North Siders.

Specifically, Taillon was asked whether new teammates Ryan Pressly and Kyle Tucker -- both longtime teammates of Bregman¡¯s with the Astros -- had clued the pitcher in on any recruiting they were doing behind the scenes.

¡°I don¡¯t know about recruiting,¡± Taillon finally said. ¡°But I know those guys speak very highly of him. And I have definitely heard them communicate that out loud.¡±

Pressly, who was acquired from Houston via trade last month to step in as an experienced closer for the Cubs¡¯ bullpen, has not been shy about saying how much Bregman could impact the room and lineup. The veteran pitcher said as much in his introductory Zoom chat with reporters, then he doubled down after Tuesday¡¯s workout at Chicago¡¯s spring complex.

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Sitting in the bleachers next to Field 1, Pressly again praised the 30-year-old Bregman for his ability to help foster a winning environment. And as Bregman remains on the open market, Pressly acknowledged that he has checked in periodically with his friend for updates.

¡°I don¡¯t think it¡¯s recruiting,¡± Pressly said. ¡°It¡¯s just more of like, ¡®Hey, how are you doing? What¡¯re you hearing?¡¯ Stuff like that. I don¡¯t [need to] be like, ¡®Hey, come here, come here.¡¯ Would I like to play with him? 1,000% -- I would love to play with him. But like I said, he¡¯s got to make decisions for his family as well. Whatever decision he makes, I¡¯m going to support him.¡±

Pressly laughed when asked if he has been in the ear of Cubs president of baseball operations Jed Hoyer about adding Bregman.

¡°Jed¡¯s got his hands full," Pressly said. "I¡¯m just trying to stay in my lane."

The Cubs remain linked to Bregman in various reports and rumors -- with the Astros, Tigers and Red Sox among teams also reportedly in the hunt -- but they have more than on-field factors to weigh.

Bregman is among the players who declined a qualifying offer for 2025, so signing him would include an extra cost for Chicago. Because they went over the first Competitive Balance Tax threshold last year, if the Cubs signed Bregman, they would forfeit their second- and fifth-highest picks in the 2025 Draft and would lose $1 million in international bonus pool money for signing Bregman.

Chicago is also trying to stay under the first CBT threshold this year ($241 million). The team is estimated to have just north of $30 million in CBT payroll flexibility, so signing Bregman could take some creativity. It feels similar to when the Cubs re-signed Cody Bellinger last spring via a three-year deal that included multiple opt-out clauses.

¡°I¡¯m sure he would¡¯ve wanted to sign the day after the season ended,¡± Pressly said of Bregman. ¡°But that¡¯s the nature of free agency. We¡¯ll see what happens.¡±

During his spring-opening media session on Sunday, Hoyer said it was ¡°unclear¡± if the Cubs were done adding to the roster, adding that he is always on the hunt for opportunistic moves. Beyond third, the Cubs might also be in the market for a backup first baseman (The Athletic reported they have kept tabs on Justin Turner) and have not ruled out seeking more pitching.

¡°We¡¯re not done. I don¡¯t think you ever consider yourself done building a roster -- big or small,¡± Cubs manager Craig Counsell said on Tuesday. ¡°I would say we¡¯re still always looking at options out there, for sure. Absolutely.¡±

Without Bregman, the Cubs¡¯ leading contender for third base is top prospect Matt Shaw, ranked No. 19 on MLB Pipeline¡¯s Top 100 list. Hoyer said the Cubs would not be ¡°anointing¡± the rookie, but giving him a chance to earn the job.

Bregman would bring a player who has made two All-Star teams, finished in the top five in MVP voting twice, won his first Gold Glove Award last season and has played in 99 postseason games. That includes seven trips to the American League Championship Series, four World Series appearances and a pair of rings.

¡°He¡¯s a special guy -- a special guy to have in the clubhouse as well,¡± Pressly said. ¡°The Astros organization would tell you the same thing. The guy, he¡¯s super competitive. He wants to win -- it doesn¡¯t matter what it¡¯s at. He wants to be that guy. To have him in this clubhouse would be pretty special.¡±